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Chemical Structure| 1670-14-0 Chemical Structure| 1670-14-0
Chemical Structure| 1670-14-0

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Benzamidine hydrochloride is an reversible competitive inhibitor of trypsin-like serine proteases, with Kis of 97 µM, 21 µM, 20 µM and 110 µM for uPA, trypsin, tryptase and factor Xa, respectively.

Synonyms: Benzamidine (hydrochloride); Benzamidine HCl

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Product Details of Benzamidine HCl

CAS No. :1670-14-0
Formula : C7H9ClN2
M.W : 156.61
SMILES Code : N=C(N)C1=CC=CC=C1.[H]Cl
Synonyms :
Benzamidine (hydrochloride); Benzamidine HCl
MDL No. :MFCD00013025
InChI Key :LZCZIHQBSCVGRD-UHFFFAOYSA-N
Pubchem ID :80289

Safety of Benzamidine HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Benzamidine HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1670-14-0 ]
  • Downstream synthetic route of [ 1670-14-0 ]

[ 1670-14-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 1670-14-0 ]
  • [ 92385-43-8 ]
  • [ 85386-14-7 ]
YieldReaction ConditionsOperation in experiment
75% With sodium In ethanol Example 32
2-PHENYLPYRIMIDINE-5-CARBONYL CHLORIDE
A solution of ethyl 3-N,N-dimethylamino-2-formylacrylate (4.0 g, 23 mmol) (Arnold, Coll. Czech. Chem. Commun. 26:3051, 1961), benzamidine hydrochloride (4.0 g, 26 mmol) and sodium (0.65 g, 28 mmol) in EtOH (40 mL) was heated at reflux for 1 h.
The solution was filtered and concentrated and the residue partitioned between EtOAc and dilute HCl (10percent).
The organic layer was dried (Na2 SO4), and concentrated to give ethyl 2-phenylpyrimidine-5-carboxylate (4.0 g, 75percent yield); m.p. >220° C. (dec.).
References: [1] Journal of medicinal chemistry, 2000, vol. 43, # 21, p. 3995 - 4004.
[2] Patent: US5811428, 1998, A, .
  • 2
  • [ 80370-42-9 ]
  • [ 1670-14-0 ]
  • [ 85386-14-7 ]
References: [1] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 96 - 107.
  • 3
  • [ 1670-14-0 ]
  • [ 85386-14-7 ]
References: [1] Journal of Organic Chemistry, 1996, vol. 61, # 7, p. 2470 - 2483.
  • 4
  • [ 25023-37-4 ]
  • [ 1670-14-0 ]
  • [ 864377-28-6 ]
YieldReaction ConditionsOperation in experiment
58% With potassium carbonate In ethanol; 1-ethoxyethanol at 90℃; for 24 h; a); 5.45 g (34.8 mmol) benzamidine hydrochloride hydrate and 4.10 g (73.1 mmol) po- tassium carbonate in 50 ml ethanol are stirred at 90 °C under dry air. 20.0 g (69.7 mmol) (E)-1-(3-bromophenyl)-3-phenyl-prop-2-en-1-one in 20 ml hot ethoxy-ethanol are added slowly. After 24 h the reaction mixture is cooled to 25 °C, the product is filtered off, washed with ethanol, water and again ethanol and is used without further purification in step b) (
References: [1] Patent: WO2012/80052, 2012, A1, . Location in patent: Page/Page column 48.
[2] Patent: US2012/149904, 2012, A1, . Location in patent: Page/Page column 43.
  • 5
  • [ 3132-99-8 ]
  • [ 1670-14-0 ]
  • [ 98-86-2 ]
  • [ 864377-28-6 ]
YieldReaction ConditionsOperation in experiment
26%
Stage #1: With sodium methylate In methanol; ethanol at 20℃; for 9 h; Inert atmosphere; Reflux
Stage #2: With sodium hydroxide In methanol; ethanol at 70℃; for 5 h;
3-bromobenzaldehyde (18.5 g, 100 mmol), acetophenone (12.0 g, 100 mmol), 1N-sadium methoxide/methanol solution (10 ml) and ethanol (200 ml) were stirred for five hours at the room temperature under an Ar gas atmosphere. Subsequently, the reactant mixture was heated and stirred for another four hours at a reflux temperature. Next, benzamidine hydrochloride (9.4 g, 60 mmol) and sodium hydroxide (8.0 g, 200 mmol) were added thereto and stirred for five hours at 70 degrees C. After the reaction, the reactant mixture was filtered to separate an extract. The extract was refined by silica-gel column chromatography (a developing solvent: dichloromethane) to provide an intermediate body X6 as a white solid. A yield of the intermediate body X6 was 10.1 g and a yield rate thereof was 26percent.
References: [1] Patent: US2016/343955, 2016, A1, .
[2] Patent: EP2489664, 2012, A1, . Location in patent: Page/Page column 46-47.
 

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